This article is an investigation of two apparently contradictory impulses in Oakeshott’s writings about liberal education. On the one hand, he implied that it was primarily ‘aesthetic’, something undertaken for its own sake with no practical consequences. On the other hand, he often implied that a student might undergo a moral transformation in the process of becoming educated. This article attempts to reconcile both these ideas in Oakeshott’s thought, and to show that they are coherent within the German Bildung tradition.